141192-98-5

Upstream product

• 55174-91-9 (-)-1,2-O-isopropylidene-5-O-pivaloyl-α-D-xylofuranose 
• 55174-92-0 1,2-O-isopropylidene-5-O-2,2-dimethylpropanoyl-α-D-erythro-pent-3-ulofuranose 
• 532-20-7 D-xylofuranose 
• 141192-92-9 1-O-(tert-butyldimethylsilyl)-5-(2,2-dimethylpropanoyl)-3-ethynyl-3-O-methyl-α-D-ribofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 141192-88-3 2,2-Dimethyl-propionic acid (3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-6-trimethylsilanylethynyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 
• 141192-90-7 5-(2,2-dimethylpropanoyl)-3-ethynyl-3-O-methyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 141192-89-4 5-(2,2-dimethylpropanoyl)-3-ethynyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 147700-83-2 5-(2,2-dimethylpropanoyl)-3-ethynyl-3-O-methyl-D-ribofuranose 
• 141192-96-3 (2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-3-methoxy-4-pentyn-1,2-diol 
• 128878-88-6 (Z)-5-<3-(Trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl trifluoromethanesulfonate 
• 87-72-9 D-Xylose 
• 141192-97-4 (2S,3S)-3-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-3-methoxy-5-<(5Z)-5-<(3-trimethylsilyl)-2-propynylidene>-1-cyclopenten-1-yl>-4-pentyn-1,2-diol 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

Synthetic studies on the compounds related to neocarzinostatin chromophore. 3. Novel synthesis of a chiral cyclic dienediyne system

Novel synthesis of the chiral 10-membered dienediynes (2 and 3) related to neocarzinostatin chromophore was accomplished by utilizing cyclization of an epoxy acetylene as a key step. The epoxy acetylene was prepared from the (Z)-dienediyne diol which could be obtained by coupling reaction of the (Z)-enol triflates (5) with the optically active acetylene diol (25) derived from D-xylose.

Novel Synthesis of a Chiral Cyclic Dienediyne System Related to the Neocarzinostatin Chromophore

By succesive treatment with lithium bistrimethylsilylamide and boron trifluoride-diethyl ether in tetrahydrofuran at - 78 deg C optically active (Z)-dienediyne epoxide 20 prepared from D-xylose and (Z)-enol triflate 16 is found to undergo smooth cyclization to afford the title compound.